WO2015059716A2 - Improved process for the preparation of ((3s,5r)-5-((1h-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methyl-4-methylbenzenesulfonate - Google Patents

Improved process for the preparation of ((3s,5r)-5-((1h-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methyl-4-methylbenzenesulfonate Download PDF

Info

Publication number
WO2015059716A2
WO2015059716A2 PCT/IN2014/000673 IN2014000673W WO2015059716A2 WO 2015059716 A2 WO2015059716 A2 WO 2015059716A2 IN 2014000673 W IN2014000673 W IN 2014000673W WO 2015059716 A2 WO2015059716 A2 WO 2015059716A2
Authority
WO
WIPO (PCT)
Prior art keywords
formula
compound
difluorophenyl
solvents
tetrahydrofuran
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/IN2014/000673
Other languages
English (en)
French (fr)
Other versions
WO2015059716A3 (en
Inventor
Srinivasan Thirumalai Rajan
Sajja Eswaraiah
Maramreddy Sahadeva Reddy
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
MSN Laboratories Pvt Ltd
Original Assignee
MSN Laboratories Pvt Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by MSN Laboratories Pvt Ltd filed Critical MSN Laboratories Pvt Ltd
Priority to US15/031,536 priority Critical patent/US20160237066A1/en
Priority to EP14855720.0A priority patent/EP3060559A4/en
Publication of WO2015059716A2 publication Critical patent/WO2015059716A2/en
Publication of WO2015059716A3 publication Critical patent/WO2015059716A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
    • C07D263/26—Oxygen atoms attached in position 2 with hetero atoms or acyl radicals directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

  • the fourth aspect of the present invention is to provide a process for the preparation of (2R,4R)-2-(2,4-difluorophenyl)-2-(iodome&yl)-4-( ty ⁇ of formula- 10 and also provides its novel crystalline form.
  • Figure 3 Illustrates the IR spectrum of crystalline form-M of (2R,4R)-2-(2,4-difluorophenyl)-2- (iodomemyl)-4-(trityloxymethyl)tetrahydrofuran.
  • suitable "coupling agent" used in the present invention refers to ⁇ , ⁇ '- dicyclohexylcarbodiimide (DCC), ⁇ , ⁇ '-diisopropylcarbodiimide (DIC), l-ethyl-3-(3- dimethylaminopropyl)carbodiimide hydrochloride (EDC.HC1), alkyl or aryl chloroformates such as ethyl chloroformate, benzylchloroformate, diphenyl phosphoroazidate (DPP A), thionyl chloride, oxalyl chloride, phosphorous oxychloride, phosphorous pentachloride, 4-methyl-2- oxopentanoyl chloride (i-BuCOCOCl), benzotriazol-l-yl-oxytripyrrolidino phosphonium hexafluorophosphate (PyBOP), methane sulfonyl chloride and
  • the suitable deprotecting agent is selected from mineral acid such as sulfuric acid,
  • step-a) & step-d) the suitable base and the suitable solvents used are same as defined in step-g) and step-j) of the first aspect of the present invention.
  • step-a) is selected from chloro solvents, ketone solvents, ester solvents, alcoholic solvents and the mixtures thereof and the suitable anti-solvent used in step-d) is selected from ether solvents.
  • Dichloromethane 1000 ml was added to (R)-3-(4-(2,4-difluorophenyl)pent-4-enoyl)-4- phenyloxazolidin-2-one (100 gm) at 25-30°C under nitrogen atmosphere. Cooled the reaction mixture to - 10-15°C. Titanium tetrachloride solution in dichloromethane (50 ml) was slowly added to the reaction mixture at -10-15°C. Diisopropyl ethylamine (45.61 gm) was added to the reaction mixture at -10-15°C and stirred for 1 hour at the same temperature.
  • Example-7 Preparation of ((3R,5R)-5-(2,4-difluorophenyl)-5-(iodomethyl) tetrahydro furan-3-yI)methanol (Formula- 9)
  • a mixture of (3S,5R)-5-(2,4-difluorophenyl)-5-(iodomethyl)tetrahydrofuran-3-carboxylic acid (250 gm) and tetrahydrofuran (500 ml) were slowly added to a pre-cooled solution of tetrahydrofuran (500 ml) and sodium borohydride (52 gm) at 0-5°C.
  • Example-20 Preparation of 4-(4-(4-(4-(((3R,5R)-5-((lH-l,2,4-triazol-l-yl)methyl)-5-(2,4- difluorophenyl)tetrahydrofuran-3-yl)methoxy)phenyI)piperazin-l-yl)phenyl)-l-((2S,3S)-2- (benzyloxy)pentan-3-yl)-lH-l,2,4-triazol-5(4H)-one

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/IN2014/000673 2013-10-22 2014-10-21 Improved process for the preparation of ((3s,5r)-5-((1h-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methyl-4-methylbenzenesulfonate Ceased WO2015059716A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US15/031,536 US20160237066A1 (en) 2013-10-22 2014-10-21 Improved process for the preparation of ((3s,5r)-5-((1h-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methyl-4-methylbenzenesulfonate
EP14855720.0A EP3060559A4 (en) 2013-10-22 2014-10-21 Improved process for the preparation of ((3s,5r)-5-((1h-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methyl-4-methylbenzenesulfonate

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN4757/CHE/2013 2013-10-22
IN4757CH2013 IN2013CH04757A (enrdf_load_stackoverflow) 2013-10-22 2014-10-21

Publications (2)

Publication Number Publication Date
WO2015059716A2 true WO2015059716A2 (en) 2015-04-30
WO2015059716A3 WO2015059716A3 (en) 2015-07-02

Family

ID=52993715

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2014/000673 Ceased WO2015059716A2 (en) 2013-10-22 2014-10-21 Improved process for the preparation of ((3s,5r)-5-((1h-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methyl-4-methylbenzenesulfonate

Country Status (4)

Country Link
US (1) US20160237066A1 (enrdf_load_stackoverflow)
EP (1) EP3060559A4 (enrdf_load_stackoverflow)
IN (1) IN2013CH04757A (enrdf_load_stackoverflow)
WO (1) WO2015059716A2 (enrdf_load_stackoverflow)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105440022A (zh) * 2015-12-31 2016-03-30 重庆威鹏药业有限公司 泊沙康唑主环的制备方法
CN105606736A (zh) * 2016-01-27 2016-05-25 重庆华邦制药有限公司 分离测定泊沙康唑中间体z1及其有关物质的方法
CN106317032A (zh) * 2015-06-15 2017-01-11 重庆圣华曦药业股份有限公司 一种制备高纯度的泊沙康唑的方法
CN106397417A (zh) * 2016-08-30 2017-02-15 甘肃皓天化学科技有限公司 用于制备泊沙康唑的中间体的制备方法
WO2017032908A1 (en) 2016-07-08 2017-03-02 Synthon B.V. Pharmaceutical composition comprising amorphous posaconazole
WO2017051342A1 (en) 2015-09-23 2017-03-30 Biocon Limited Crystalline forms of posaconazole intermediate and process for the preparation of amorphous posaconazole
JP2019507189A (ja) * 2016-03-04 2019-03-14 ゼァージァン アウスン ファーマシューティカル カンパニー リミテッドＺｈｅｊｉａｎｇ Ａｕｓｕｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌ Ｃｏ．， Ｌｔｄ． ポサコナゾール、組成物、中間体、並びにその製造方法及び使用
CN111675702A (zh) * 2020-04-23 2020-09-18 陕西博森生物制药股份集团有限公司 一种泊沙康唑的制备方法
CN113666915A (zh) * 2021-08-27 2021-11-19 江苏海洋大学 一种泊沙康唑中间体的制备方法
CN117510380A (zh) * 2024-01-08 2024-02-06 寿光诺盟化工有限公司 一种苯磺酸酯的制备方法

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019077627A1 (en) * 2017-10-16 2019-04-25 Metrochem Api Pvt Ltd. PROCESS FOR PRODUCING POSACONAZOLE
US20220001295A1 (en) * 2018-11-19 2022-01-06 PREM ANAND MUKUND Honavar An improved process to increase the performance on filtrate extention
CN109187824A (zh) * 2018-11-30 2019-01-11 无锡福祈制药有限公司 一种泊沙康唑的高效液相色谱分析方法
CN112898279A (zh) * 2019-11-19 2021-06-04 爱之源生物科技有限公司 一种高纯度的泊沙康唑的精制方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5403937A (en) * 1993-04-30 1995-04-04 Schering Corporation Process for preparing intermediates for the synthesis of antifungal agents
WO2009141837A2 (en) * 2008-05-21 2009-11-26 Ind-Swift Laboratories Limited Process for preparing posaconazole and intermediates thereof
BR112012029227B1 (pt) * 2010-05-19 2020-01-07 Sandoz Ag Processo para a preparação de um composto quiral, composto quiral e uso de um composto
CN103635465A (zh) * 2011-06-16 2014-03-12 桑多斯股份公司 制备手性化合物的方法
US9102664B2 (en) * 2011-09-19 2015-08-11 Msn Laboratories Private Limited Process for the preparation of triazole antifungal drug, its intermediates and polymorphs thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of EP3060559A4 *

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106317032A (zh) * 2015-06-15 2017-01-11 重庆圣华曦药业股份有限公司 一种制备高纯度的泊沙康唑的方法
US10927102B2 (en) 2015-09-23 2021-02-23 Biocon Limited Crystalline forms of posaconazole intermediate and process for the preparation of amorphous posaconazole
JP7054381B2 (ja) 2015-09-23 2022-04-13 バイオコン・リミテッド 結晶形態のポサコナゾール中間体および非晶質ポサコナゾールの調製のためのプロセス
RU2750898C2 (ru) * 2015-09-23 2021-07-05 Биокон Лимитед Кристаллические формы промежуточного соединения позаконазола и способ получения аморфного позаконазола
WO2017051342A1 (en) 2015-09-23 2017-03-30 Biocon Limited Crystalline forms of posaconazole intermediate and process for the preparation of amorphous posaconazole
KR20180055851A (ko) 2015-09-23 2018-05-25 바이오콘 리미티드 포사코나졸 중간체의 결정질 형태들 및 비정질 포사코나졸의 제조방법
JP2018528247A (ja) * 2015-09-23 2018-09-27 バイオコン・リミテッドＢｉｏｃｏｎ Ｌｉｍｉｔｅｄ 結晶形態のポサコナゾール中間体および非晶質ポサコナゾールの調製のためのプロセス
EP3353169A4 (en) * 2015-09-23 2019-05-22 Biocon Limited CRYSTALLINE FORMS OF A POSACONAZOOL PRODUCT AND METHOD FOR THE PREPARATION OF AMORPHIC POSACONAZOLE
US10457668B2 (en) 2015-09-23 2019-10-29 Biocon Limited Crystalline forms of posaconazole intermediate and process for the preparation of amorphous posaconazole
CN105440022A (zh) * 2015-12-31 2016-03-30 重庆威鹏药业有限公司 泊沙康唑主环的制备方法
CN105606736A (zh) * 2016-01-27 2016-05-25 重庆华邦制药有限公司 分离测定泊沙康唑中间体z1及其有关物质的方法
JP2019507189A (ja) * 2016-03-04 2019-03-14 ゼァージァン アウスン ファーマシューティカル カンパニー リミテッドＺｈｅｊｉａｎｇ Ａｕｓｕｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌ Ｃｏ．， Ｌｔｄ． ポサコナゾール、組成物、中間体、並びにその製造方法及び使用
WO2017032908A1 (en) 2016-07-08 2017-03-02 Synthon B.V. Pharmaceutical composition comprising amorphous posaconazole
CN106397417A (zh) * 2016-08-30 2017-02-15 甘肃皓天化学科技有限公司 用于制备泊沙康唑的中间体的制备方法
CN111675702A (zh) * 2020-04-23 2020-09-18 陕西博森生物制药股份集团有限公司 一种泊沙康唑的制备方法
CN113666915A (zh) * 2021-08-27 2021-11-19 江苏海洋大学 一种泊沙康唑中间体的制备方法
CN113666915B (zh) * 2021-08-27 2022-08-16 江苏海洋大学 一种泊沙康唑中间体的制备方法
CN117510380A (zh) * 2024-01-08 2024-02-06 寿光诺盟化工有限公司 一种苯磺酸酯的制备方法
CN117510380B (zh) * 2024-01-08 2024-04-05 寿光诺盟化工有限公司 一种苯磺酸酯的制备方法

Also Published As

Publication number Publication date
US20160237066A1 (en) 2016-08-18
EP3060559A2 (en) 2016-08-31
WO2015059716A3 (en) 2015-07-02
IN2013CH04757A (enrdf_load_stackoverflow) 2015-04-24
EP3060559A4 (en) 2017-05-24

Similar Documents

Publication Publication Date Title
WO2015059716A2 (en) Improved process for the preparation of ((3s,5r)-5-((1h-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methyl-4-methylbenzenesulfonate
EP2758385B1 (en) Process for the preparation of triazole antifungal drug, its intermediates and polymorphs thereof
US20080021213A1 (en) Novel process for the preparation of linezolid and related compounds
US9718779B2 (en) Intermediate and polymorphs of 1-(4-methoxypheny1)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5,6,7-tetra hydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide and process thereof
WO2013186792A2 (en) Process for the preparation of (5-methyl-2-oxo-l,3-dioxoi-4-vl)methvl 2- ethoxv-l-{[2'-(5-oxo-4,5-dihvdro-l,2,4-oxadiazol-3-vl)biphenyi-4-vl]methyl}- lh-benzimidazole-7-carboxyiate and its salts
WO2011101861A1 (en) Process for preparation of dpp-iv inhibitors
US20170029398A1 (en) Process for the preparation of (1s)-1,5-anhydro-1-c-{4-chloro-3-4[(4-ethoxyphenyl)methyl]phenyl]-glucitol and its solvate thereof
JP5812985B2 (ja) ５員複素環化合物シクロペンタ［ｃ］ピロリルアルキルカルバメート誘導体、これらの調製およびこれらの治療上の使用
EP3481807A1 (en) Novel process for the preparation of 2-{4-[(5,6-diphenyl pyrazin-2-yl)(isopropyl)amino]butoxy}-n-(methylsulfonyl)acetamide and novel polymorphs thereof
WO2018104953A1 (en) Improved process for the preparation of 7-{4-[4-(2,3-dichlorophenyl)-piperazin-1-yl]butoxy}-2oxo-3,4-dihydro-2h-quinolin-1-yl)methyl dodecanoate
US10633372B2 (en) Process for the preparation of amorphous (1S)-1,5-anhydro-1-[3-[[5-(4 fluorophenyl)-2-thienyl]-4-methylphenyl]-D-glucitol and its polymorphs thereof
WO2014188453A2 (en) Novel process for the preparation of 2-[4-(2-{4-[1-(2-ethoxyethyl)-1h-benzimidazol-2-yl]-1-piperidinyl}ethyl) phenyl]-2-methylpropanoic acid
CA2743558C (fr) Derives de carbamates d'alkyl-heterocycles, leur preparation et leur application en therapeutique
US6686363B2 (en) Cyclopropyl containing oxazolidinone antibiotics and derivatives thereof
EP1467977A1 (en) Novel antibacterial compounds:process for their preparation and pharmaceutical compositions containing them.
US11236050B2 (en) Polymorphs of 4-[3-chloro-4-(n′-cyclopropyl ureido)phenoxy] -7-methoxyquinoline-6-carboxamide, its salts and process for the preparation thereof
EP2814819A1 (en) Process for preparing 4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid compounds
WO2004101531A1 (en) Antiinfective 1,2,3-triazole derivatives, process for their preparation and pharmaceutical compositions containing them
US20220306650A1 (en) Process and polymorphic forms of bictegravir and its pharmaceutically acceptable salts or co-crystals thereof
WO2018134842A1 (en) Process for the preparation of carbamic acid, n,n'-[[1,1'-biphenyl] -4,4'-diylbis]- 1 h-imidazole-5,2 diyi-(2s)-2,1-pyrrolidinediyl[(1 s)-1-(1-methylethyl)-2-oxo-2,1-ethanediyl]]] bis-,c,c'-dimethyl ester and its salts and polymorphs
WO2024257116A1 (en) Novel polymorphic forms of asciminib and its pharmaceutical salts thereof
WO2016193997A2 (en) Process for the preparation of 6-(3-chloro-2-fluorobenzyl)-1-[(2s)-1-hydroxy-3-methylbutan-2-yl]-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid and pharmaceutically acceptable salts thereof
WO2017098522A1 (en) Crystalline polymorph of n-(2,2,2-trifluoroethyl-9-[4-[r4-r[[[i4'- (trifluoromethyl) [ 1,1 ' -biphenyl] -2-yl] carbonyl] amino] -1 -piperidinyl] butyl] -9h- fluorene-9-carboxamide methanesulfonate and process for preparation thereof
WO2016142954A2 (en) IMPROVED PROCESS FOR THE PREPARATION OF [3R,5R]-2-FLUOROPHENYL-β,δ- DIHYDROXY-5-(1-METHYLETHYL)-3-PHENYL-4-[(2-HYDROXYPHENYLAMINO)- CARBONYL]-1H-PYRROLE-1-HEPTANOIC ACID, SODIUM SALT

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 14855720

Country of ref document: EP

Kind code of ref document: A2

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 15031536

Country of ref document: US

REEP Request for entry into the european phase

Ref document number: 2014855720

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 2014855720

Country of ref document: EP